DE2311897A1 - N-substd phenylamines prepn - as herbicides alone or with other acceptable herbicides - Google Patents

Abstract

Cmpds. (I) (where R is H, halogen, NO2, Hal3C, 1-7C alkyl or -alkoxy; R' is H, mono-di- or trihaloacetyl; R" is 1-7C-alkylene or 2-7C alkylidene; Q is carboxy, salified carboxy, a carboxy ester with a 1-7C-alkanol, carboxy amide or carbohydrazides opt. N substd. by 1-7C alkyl or aryl) are prepd. by reacting a substd. phenylamine with a halo alkanoic acid deriv. (I) may form compsns. with other herbicides. Specif claimed is N-(2,6-diethylphenyl)glycine prepd. from 2,6-diethylphenylamine and ethyl bromoacetate.

Description

N-Substituted N-Phenylamines and Herbicidal Agents The invention relates to aromatic amines for weed control as well as herbicides that contain these amines alone or in conjunction with other herbicidal active ingredients.

The invention relates to new, N-substituted N-PhEylamines of the general formula (I) in which the substituents R are identical or different and denote a hydrogen or halogen atom, a nitro or trihalomethyl group, a C1-7-alkyl or C1-7-alkoxy group, R 'is a hydrogen atom, a mono-, di- or trihaloacetyl group , R ″ represents a C17-alkylene or C2-7-alkylidene radical and Q represents a carboxyl group, a salt or a C1-7-alkanol ester thereof, an amide, mono- or disubstituted amide radical, the substituents being C1-7-alkyl radicals or aryl radicals are, or a C-bohydrazide or 1-substituted carbohydrazide radical with C1-7-alkyl radicals or aryl radicals as substituents.

The invention also relates to heibicide agents which are a mixture from an N-phenylamine of the general formula (I) and an application aid contain.

Application auxiliaries are generally inert Fabrics that. facilitate the distribution or dispersion of the phytotoxic mixture, when this is applied to the ground or to the leaves of unwanted plants will. Examples of application auxiliaries are thinners, carriers, Extenders, surfactants, adhesives, distribution aids or substances that reduce the wind regulate.

The invention also relates to a method for combating grassy weeds, which is characterized by having an effective amount of an N-phenylamine of the general formula (I) or a herbicib prepared therewith Applies means to the location of the weeds mentioned.

The N-phenylamines of the general formula (I) act both before Emergence as well as after emergence toxic to grass-like weeds, namely at concentrations at which grass-like weeds are killed or in their Growth are inhibited, but many desirable fruit plants are relatively unaffected of this stay. Broad-leaved weeds, however, are generally among these Econcentrations of compounds more resistant than grassy weeds.

That is why it is applied when applying the N-phenylamines of the invention The common location of both weed species is desired, sometimes others Apply herbicides that kill broad-leaved weeds or in their growth inhibit. These other herbicides should have essentially no diminution in effectiveness the N-phenylamines affect the grass-like weeds and are allowed to deal with the Do not combine N-phenylamines, as this has undesirable effects on growth can arise from fruit plants.

The invention also relates to herbicide combinations for Control of both grassy and broadleaf weeds that are a mixture from an N-phenylamine of the general formula (I) and Norea, Fluometuron, Chloroxuron, Contain diuron, linuron, fenuron, atrazine or pyrazone.

It concerns Norea, Fluometuron, Chbroxuron, Diuron and Linuron common herbicides known to be broad-leaved on the opposite side Weeds are toxic. They are not yet in connection with the new, substituted ones N-2henylamines of the invention have been used.

Norea is the common name for 3- (3a, 4,5,6,7,7a-Eexahydro-4,7-methanoindan-5-yl) -1,1-dimethylurea. This compound and its preparation are described in US Pat. No. 3,304,167. That Product is commercially available under the name "Herban".

Fluometuron is the common name for N- (3-trifluoromethylphenyl) -N ' , N '-dimethylurea. This compound and its preparation are set out in U.S. Patent 3 134 665 described. The product is commercially available under the name 'Cotorant' available.

Chloroxuron is the common name for 3-p- (p-chlorophenoxy) -pheny 1,1-dimethylurea. This compound and a process for making it are in U.S. Patent 3,060,235. The product is commercially available under the name "Tenoran" available.

Diuron is the common name for 3- (3,4-dichlorophenyl) -1,1-dimethylurea. This compound and its preparation are described in US Pat. No. 2,655,445.

The product is commercially available under the name "Karmex".

Linuron is the common name for 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea. This compound and its preparation are described in US Pat. No. 2,960,534.

The product is commercially available under the name "Lorox".

The invention also relates to a method for combating both grassy and broad-leaved weeds, which is characterized by it is to apply an effective amount of the foregoing to the location of the weeds Herbicide combination applies.

The substituted N-phenylamines of the invention are around brown, yellow-brown and yellow substances that are either liquid or liquid at 20 to 25 ° C are firm. The esters of the invention are insoluble in water, but they are in soluble in solvents such as acetone or benzene to the extent necessary for use as a herbicide is sufficient. On the other hand are the acids, salts, amides and hydrazides of the invention in water at least to such an extent soluble, that the active ingredients are suitable for use in herbicides.

The N-phenylamines of the general formula (I) can be prepared by adding the corresponding phenylamine of the general formula (II) in a liquid reaction medium which contains a base such as salium hydroxide in which R has the aforementioned meaning with a haloalkanoic acid or an ester of the general formula (III) in which R 'has the aforementioned meaning and X represents a halogen atom, is reacted to form those compounds of the class in which R' is a hydrogen atom, These compounds are mixed with mono-, di- and trihaloacetyl halides of the general formula (IV) in which X has the aforementioned meaning and n has a value from 0 to 2, reacted to form the desired N-phenylamines of the invention.

The herbicidal compositions of the invention are applied so that applying it to the soil or leaves of the weeds in a conventional manner.

The amount of herbicidal agents used should be so high that depending on the application method and the desired success, an effective one Concentration of the phytotoxic material in the soil, on the weed leaves or arises both in the soil and on the leaves.

Im Ball deals with herbicidal agents that are usually solid the application auxiliaries are generally an inert solid in a finely divided state. In some embodiments, these herbicidal agents it is granules, in other cases dispersible powders or dusts The granules can be produced by coating, impregnating or incorporation will.

The coated granules are produced in such a way that one can be wetted Powder or milled powder of the phytotoxic aterial on a granulated The backing material is dusted on either before or after it has been dusted with an adhesive is mixed. Water, oils or hydrocarbons, alcohols, Glycols, aqueous gums or waxes and mixtures thereof are used. Examples for granulated carriers are attapulgite, corn on the cob, vermiculite, walnut shells as well as almost all granulated, mineral or organic substances that contribute to the desired size are shredded. Generally makes the phytotoxic material about 2 to 20% by weight of the granulated agent, the adhesive about 5 to 40% by weight of the agent and the granulated carrier generally about 60 to 93% by weight of the remedy.

The impregnated, granulated agents are manufactured so that the phytotoxic material is dissolved in a solvent or melted and then the liquid thus formed is sprayed or poured onto the granulated carrier material. The solvent can be evaporated or left in the middle.

The phytotoxic material impregnates the granulated dSS particles Carrier material. Examples of granulated carrier materials are already 1m in view on listed the coated type of granulated agent, the phytotoxic mixture generally makes up about 2 - 20% by weight of the agent, while the proportion of the granulated carrier material is about 80 - 98 ew.-0 / o, based on the agent.

For the manufacture of the incorporated, granulated agents, the phytotoxic Mixture with an inert, finely divided solid such as clay, carbon black or burnt Plaster of paris, mixed and combined with water or another vaporizable liquid to form one Mashed porridge. The porridge then becomes a solid layer or cake dried, broken or crushed and sieved into the desired grain size brought. In other embodiments, the slurry becomes closed in a pan deformed into a granulate, the water or solvent subsequently being removed will. In another process, the pulp is pressed into bars through nozzles, which are cut into small pieces. In the case of the incorporated type, the granulated Agent generally makes up about 2-50% by weight of the phytotoxic mixture and that remainder of the carrier material is about 50-98% by weight, based on the agent.

In all granulated embodiments of the dispersible, herbicidal Means of the invention can also contain various additives in lower concentrations, based on the carrier material.

In the case of the powdery or rod-like, dispersible, solid, herbicidal ones For the purposes of the invention, the carrier is generally a dispersible, inert one Solid, like clay.

Further suitable dispersible solids are e.g. Talc, attapulgite, Pyrophylite, diatomaceous earth, kaolin, aluminum magnesium silicate, montmorillonite, puller earth or sawdust. Provided that the solid dispersible agents are dispersible in air are, they can be used as dusts. If they are dispersible in water, they are commonly referred to as wettable powders. Those dispersible in water Agents preferably contain emulsifiers, such as surfactants, in sufficient concentrations in order to be able to form a suspension with the desired degree of stability, if the Agent is mixed with an appropriate amount of water. A typical, dispersible, Solid agent of the invention generally contains about 10-80% by weight of phytotoxic Mixture, about 20-90% by weight solid carrier material and, if emulsifiers are present are, about 1 - 10 wt .-% emulsifiers.

Further specific embodiments of the herbicidal compositions of the invention are solutions of the phytotoxic mixture of the invention in inert, preferably volatile, solvents for the phytotoxic mixture. One such solution that can be regarded as a concentrate, typically contains about 10-50 wt .- / O phytotoxic mixture and about 50-90% by weight solvent. The solution can either as such, after diluting with more solvent or, provided an or several components of the phytotoxic mixture are water-insoluble, dispersed in water, or with water dispersed therein. Preferably, when the solution of the water-insoluble components are dispersed in water or Water to be dispersed therein contains the mixture of solution and water also emulsifiers in sufficient concentration to achieve a dispersion with the desired Form stability level. Typical emulsifier concentrations are around 1 - 10 % By weight, based on the concentrate. The water concentration is so high that the Concentration of the phytotoxic mixture about 0.5 10% by weight, based on the total means is.

Examples of surfactants that are found in both the liquid and the solid agents of the invention are used, the well-known surfactants of the anion active, cation active or nonionic type and include alkali (sodium or Potassium) oleate and similar soaps, amine salts of long-chain fatty acids (oleates), sulfonated animal and vegetable oils (fish oils and castor oil), sulfonated oil fractions, sulfonated acyclic hydrocarbons, sodium salts of lignosulfonic acids, Alkylnaphthalene sodium sulfonate, sodium lauryl sulfonate, disodium monolauryl phosphate, Sorbitol laurate, pentaerythritonostearate, glycerol monostearate, polyethylene oxide, ethylene oxide condensate of stearic acid, stearyl alcohol, stearylamine, rosin amines or dehydroabietylamine, Laurylamine salts, dehydroabietylamine salts, laurylpyridinium bromide, stearyltrimethylammonium bromide or cetyldimethylbenzylammonium chloride. Further examples are given in "Detergents and Emulsifiers - 1968 Annual "by John W.

McCutcheon described.

In addition to the phytotoxic mixture and the application aid contain special embodiments of these pergeable herbicidal agents Invention one or more other components, examples of which are plant growth regulators, Insecticides, acaricides, fungicides, nematocides or plant nutrients.

To determine the specific chemical structures of the N-substituted N-phenylamines of the invention it is pointed out that the C1-7-alkyl radicals both straight-chain as well as branched alkyl radicals. Examples are the Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl or pentyl group. The C1-7 alkoxy radicals include both straight-chain and branched alkoxy radicals with 1 to 7 carbon atoms. Specific examples are the methoxy, ethoxy, propoxy, Isopropoxy, butoxy, isobutoxy, tert.- Butoxy or pentoxy group. The halogen atoms are fluorine, chlorine, bromine or iodine atoms. The C1-7 alkylene radicals include both straight and branched alkylene radicals with 1 to 7 carbon atoms. Specific examples are the ethylene, propylene, 1-methylethylene, 2-methylethylene, Butylene, 1-methylpropylene, 2-methylpropylene, 3-methylpropylene, 1, 1-dimethylethylene, 1,2-dimethylethylene or 2,2-dimethylethylene group. The C2 to C7 alkylidene resis include both straight-chain and branched alkylidene radicals with 2 to 7 carbon atoms. Specific examples are the ethylidene propylidene, isopropylidene, butylidene, 1-methylpropylidene, 2-methylpropylidene or 2,2-dimethylethylidene group.

Examples of salts are ammonium salts, alkali salts (e.g.

Sodium or potassium), alkaline earth salts (e.g. calcium or magnesium) and amine salts (e.g. methylamine, diethylamine, tripropylamine, or diphenylamine). Examples for C1-7 alkanol esters are the methyl esters, ethyl esters, propyl esters or isopropyl esters. Examples of aryl radicals are the phenyl, tolyl or naphthyl group.

Specific examples of compounds represented by general formula (I) are listed below.

Compound No.Name 1 N- (p-chlorophenyl) -glycine ethyl ester 2 N- (m-chlorophenyl) -glycine ethyl ester 3 N- (o-chlorophenyl) -glycine ethyl ester 4 N-phenyl-glycine ethyl ester 5 N (2,3-dichlorophenyl) - glycine ethyl ester 6 N- (3, 4-dichlorophenyl) glycine ethyl ester 7 N- (2-chloro-4-nitrophenyl) glycine ethyl ester 8 N- (4-chloro-3-nitrophenyl) glycine ethyl ester 9 N- (2,4,5- Trichlorophenyl) glycine ethyl ester 10 N-chloroacetyl-N- (p-chlorophenyl) -glycine ethyl ester Compound No. Name 11 N-chloroacetyl-N- (m-chlorophenyl) -glycine ethyl ester 12 N-chloroacetyl-N- (o-chlorophenyl) -glycine ethyl ester 13 N-chloroacetyl-N-phenyl-glycine ethyl ester 14 N-chloroacetyl-N- (2,3-dichlorophenyl) -glycine ethyl ester 15 N-chloroacetyl-N- (3,4-dichlorophenyl) -glycine ethyl ester 16 N-chloroacetyl-N - (p-chlorophenyl) -glycine ethyl ester 17 N-chloroacetyl-N- (m-chlorophenyl) -glycine ethyl ester 18 N-dichloroacetyl-N- (o-chlorophenyl) -glycine ethyl ester 19 N-dichloroacetyl-N-phenyl-glycine ethyl ester 20 N- Dichloroacetyl-IT- (2,3-dichloropheny49glycine ethyl ester 21 N-chloroacetyl-N- (3,4-dichlorophenyl ) -glycine ethyl ester 22 N-chloroacetyl-N- (p-chlorophenyl) -glycine ethyl ester 23 N-chloroacetyl-N- (m-chlorophenyl) -glycine eth ester 24 N-chloroacetyl-N- (o-chlorophenyl) -glycine ethyl ester 25 N-chloroacetyl -N-phenyl-glycine ethyl 26 N-trichloroacetyl-N- (2,3-dichlorophenyl) -glycine ethyl ester 27 N-chloroacetyl-N- (3,4-dichlorophenyl) -glycine ethyl ester 28 N-chloroacetyl-N- (2-chloro- 4-nitrophenyl) glycine ethyl ester 29 N-chloroacetyl-N- (4-chloro-3-nitrophenyl) -glycine ethyl ester 30 N-chloroacetyl-N- (2,4,5-trichlorophenyl) -glycine ethyl ester 31 N-dichloroacetyl-ET- ( 2-chloro-4-nitrophetyl) -glycine ethyl ester 32 N-dichloroacetyl-N- (4-chloro-3-nitrophenyl) -glycine ethyl ester Compound No. Name 33 N-dichloroacetyl-N- (2,4,5-trichlorophenyl) -glycine ethyl ester 34 N-trichloroacetyl-BT- (2-chloro-4-nitrophenyl) -glycine ethyl ester 35 N-trichloroacetyl-N- (4-chloro-3-nitrophenyl) -glycine ethyl ester 36 N-trichloroacetyl-N- (2,4,5trichlorophenyl) -glycine ethyl ester 37 N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester 38 N-chloroacetyl-N- (3-chloro-2-methoxyphene yl) glycine ethyl ester 39 N-dichloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester 40 N-dichloroacetyl-N- (3-chloro-2-methoxyphenyl) -glycine ethyl ester 41 N-trichloroacetyl-N- (2, 6- diethylphenyl) glycine ethyl ester 42 N-trichloroacetyl-N- (3-chloro-2-methoxyphenyl) glycine ethyl ester 43 N- (2,6-dichlorophenyl) glycine ethyl ester 44 N- (4-chloro-2,6-dinitrophenyl) -glycine ethyl ester 45 N- (2,6-dichloro-4-nitrophenyl) -glycine ethyl ester 46 N-chloroacetyl-N- (2,6-dichlorophenyl) -glycine ethyl ester 47 N-dichloroacetyl-N- (2,6-dichlorophenyl) -glycine ethyl ester 48 N -Ttrichloroacetyl-N- (2,6-dichlorophenyl) -glycine ethyl ester 4-9 N-chloroacetyl-N- (4-chloro-2,6-dinitrophenyl) -glycine ethyl ester 50 N-trichloroacetyl-N- (4-chloro -2,6-dinitrophenyl) glycine ethyl ester 51 N-chloroacetyl-N- (2,6-dichloro-4-nitrophenyl) glycine ethyl ester 52 N-dichloroacetyl-N- (2,6-dichloro-4-nitrophenyl) glycine ethyl ester 53 N-Trichloroacetyl-N- (2,6-dichloro-4-nitrophenyl) -glycine ethyl ester Compound No., Name 54 N- (2,4-dichlorophenyl) -glycine ethyl ester 55 N-chloroacet yl-li- (2,4-dichlorophenyl) -glycine ethyl ester 56 N-dichloroacetyl-N- (2,4-dichlorophenyl) -glycine ethyl ester 57 N-trichloroacetyl-N- (2,4-dichlorophenyl) -glycine ethyl ester 58 N- (2 , 6-diethylphenyl) glycine ethyl ester 59 N-chloroacetyl-N-phenylalanine 60 N-bromoacetyl-N-phenylalalin 61 4- (N-chloroacetyl-anilino) -butyramide 62 α- (N-chloroacetyl-2 ', 6'-diethylanilino ) -acetylhydrazine 63 4- (N-trichloroacetyl-2 ', 6'-dichloroanilino) -butyric acid, sodium salt 64 4- (N-ICrichloracetyl-9', 4- '-dichloroanilino) -butyric acid 65 2- [4- (2 ', 4'-dichloroanilino) butyryl] -1-phenylhydrazine 66 N-chloroacetyl-N- (2', 41,5'-trichlorophenyl) -alanine 67 4- (N-trichloroacetylanilino) -butyric acid, ammonium salt 68 N-chloroacetyl -N- (m-trifluoromethylphenyl) -glycine ethyl ester 69 N-trichloroacetyl-N- (m-trifluoromethylphenyl) -alanine ethyl ester 70 N- (p-trifluoromethylphenyl) -glycine 71 N-chloroacetyl-N- (2,6-diethylphenyl) -alanine ethyl ester 72 N-Carboethoxyethyl-N-chloroacetyl-2,6-diethylalanine 73 N-chloroacetyl-N- (2-methyl-6-ethylphenyl) -alanine ethyl ester 74 N-Ca rboethoxyethyl-N-chloroacetyl-2-methyl-6-ethyl-aniline 75 N-chloroacetyl-N- (2,6-dimethylphenyl) -glycine 76 N-chloroacetyl-N- (2,6-dimethylphenyl) -glycine, sodium salt compound no Name 77 N-chloroacetyl-N- (2,6-dimethylphenyl) -glycine, ammonium salt 78 N-chloroacetyl-N- (2,6-dimethylphenyl) -glycine ethyl ester 79 N-chloroacetyl-N- (2,6-diethylphenyl) -glycine 80 N-chloroacetyl-N- (2,6-diethylphenyl) -glycine, sodium salt 81 N-chloroacetyl-N- (2,6-diethylphenyl) -glycine, ammonium salt 82 N-chloroacetyl-N- (2-methyl- 6-ethylphenyl) -glycine 83 ET-chloroacetyl-N- (2-methyl-6-ethylphenyl) -glycine, sodium salt 84 N-chloroacetyl-N- (2-methyl-6-ethylphenyl) -glycine, ammonium salt 85 N-chloroacetyl -N- (2-methyl-6-ethylphenyl) -glycine ethyl ester 86 N-chloroacetyl-N- (2-chloro-6-methylphenyl) -glycine 87 N-chloroacetyl-N- (2-chloro-6-methylphenyl) -glycine , Sodium salt 88 N-chloroacetyl-N- (2-chloro-6-methylphenyl) -glycine, ammonium salt 89 N-chloroacetyl-N- (2-chloro-6-methylphenyl) -glycine ethyl ester 90 N-bromoacetyl-N- (2, 6-diethylphenyl) glycine 91 N-Bro macetyl-N- (2,6-diethylphenyl) -glycine, sodium salt .92 N-bromoacetyl-IxT- (2,6-diethylphenyl) -glycine, ammonium salt 93 N-bromoacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester In the following manufacturing processes and in the examples, all percentages relate to weight, unless stated otherwise. All parts by weight are identified by m ", all parts by volume by" v "; the parts by weight (w) relate to the parts by volume (v) like the kilogram to the liter.

Manufacturing process I The N- (2,6-diethylphenyl) -glycine ethyl ester, one of the N-substituted N-phenylamines of the invention can be prepared as follows be: mixture of ethyl bromoacetate (480 w) is added dropwise while stirring a 'from 2,6-diethylaniline (429 w), potassium hydroxide (161 w) and dimethylformamide (1500 v) added. During the addition of the ethyl bromoacetate, the temperature of the rises Reaction mixture characteristically light. When the addition is complete, the The reaction mixture was stirred at 90-1100 ° C. for 1 hour.

During this time the potassium hydroxide dissolves slowly a white precipitate. The reaction mixture is cooled to 20-250 ° C. in water poured (2000 v) and extracted three times with diethyl ether (700 v). The ether extracts are combined with water, aqueous hydrochloric acid (10%), aqueous sodium hydrogen carbonate (5 Qó) and washed with water and then dried. The diethyl ether will evaporated under reduced pressure. The residue (426.8 w) typically represents a red oil. It consists essentially of N- (2,6-diethylphenyl) glycine ethyl ester.

Similarly, the other N-phenylamines of the invention, in which X 'denotes a hydrogen atom, from the corresponding anilines and haloalkanoic acids or star made.

Manufacturing process II ID-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Another N-substituted N-phenyl amine of the invention can be prepared as follows are: A solution of 2,6-diethylphenylglycine ethyl ester (531.5 w), prepared as in example 1, in benzene (2.5 v) is under Stir drop by drop with chloroacetyl chloride (306 w) followed by pyridine (196 w). During the Additions, the temperature of the reaction mixture increases characteristically from 20-250 C to about 700 C. When the additions are complete, the reaction mixture is left for three hours Stirred at 70-800 ° C., cooled to 20-250 ° C. and filtered. The filtrate will with water, aqueous hydrochloric acid (10%, aqueous sodium hydrogen carbonate (5%) and Washed with water and then dried. After evaporation of the benzene under reduced Pressure gives the desired product (711.0 w), which is typically a red Represents oil which crystallizes on standing. A typical analysis of the Product gives: N = 4.4%, Cl = 11.9%; (calc .: N, N = 4.4%, Cl = 11.3 96). That The product consists essentially of N-chloroacetyl (2,6-diethyl-phenyl) -glycine ethyl ester.

Similarly, the other N-phenylamines of the invention, in which R 'denotes a mono-, di- or trihaloacetyl group, from the corresponding Compounds of the invention in which R 'represents a hydrogen atom and the corresponding Blono-, di- and trihaloacetyl halides produced.

In the examples, German and Latin names are used for the Broods or weeds used, which are assigned as follows: Agrostemma githago Corn Cockle Alopecurus, Hordeum Foxtail Foxtail or Setaria Amaranthus Pigweed Ambrosia Rag Weed Arctium, Xanthium Burdock Oocklebur Avena Wild Oats Beta Sugar beets Brassica Mustard Mustard Brassica juncea crispifolia Curled mustard Bromus tectorum Downey Bromegrass Cassia Marylandica Ooffee weed Chenopodium album Lambs quarter Cissampelos pareira Velvet leaf Datura stramonium Jimson weed Digitaria sanguinelis Crabgrass Echinochloa crusgalli Barnyard grass Euphorbia Spurge Glycine max soybeans Soybeans Gossypium Cotton Cotton Granum Corn Hordeum Barley Ipomoea Morning glory Lathyrus odoratus. Sweat peas Lolium Rye grass Medicago sativa Alfalfa Mollugo verticillata Carpet weed Portulaca Purslane Setaria italica stramineofructa German millet Sida spinosa Teaweed Syricum (granum) Sorghum Tagetes Marigolds Triticum Wheat Wheat peas Peas Peanuts Peanuts Green Beans Snap Beans Cucumber Cucumber Millet Millet Rice Rice Beets Red beets Tomatoes Tomatoes Examples 1 - 75 The general recipe of the herbicidal agent is as follows: Ingredients Concentration Phytotoxic material 1w poly (oxyethylene) sorbitan monolaurate in which the mean oxyethylene content is 20 Mol% is 1 v toluene Iv contains the phytotoxic material in these examples the above-listed compounds No. 1 to 75. The herbicidal action of these Connections is determined by the test results listed in the table below reproduced. These test results are from normal, routine greenhouse examinations with products consisting essentially of the compounds of the invention, been received. An in Water emulsifiable concentrate prepared by taking a sample (15 w) of the product in acetone (400 V) and then a commercial emulsifier C mixture of polyoxyethylene (20) sorbitan monooleate, in which the mean content of oxyethylene is about 20Mol10, BFono- and diglycerides of fat-forming fatty acids and an antioxidant mixture that is essentially from butylated hydroxyanisole, butylated hydroxytoluene, citric acid and propylene glycol consists (20 v) adds. The liquid concentrate is then put into water dispersed and spray applied the resulting emulsion in standard test amounts.

When used after emergence (spraying of the leaves) the emulsion in an amount of 1 to 11 kg of the test product per hectare on the sprayed on growing plants in the first real leaf stage. With the plants it is millet, granum, mustard, cotton, tomatoes and marigolds.

In Table I, the specified amount refers to pounds per ace, where Amounts of 1, 2, 10 and 20 pounds per acre amounts of 1.12; 2.24; 11.2 and 22.4, respectively kg / ha.

After a predetermined time interval during which both the sprayed Plants as well as non-sprayed plants of the same age have favorable growth conditions In a greenhouse, the sprayed plants are subjected to damage and kill and compared to the non-sprayed plants. The extent the damage or destruction is rated with numbers from 0 to 10, with the rating 0 no damage or destruction and the rating 10 100 percent damage or killing the plants means.

When used before the emergence (soil germination test), the Emulsion in an amount of 2.24 and 22.4 kg of the test product per hectare on the Ground sprayed fresh with seeds of soybean, millet, granum, mustard and cotton is sown.

After you have both the sprayed, sown soil and the unsprayed Soil that is freshly sown with these seeds, regulated, favorable growth conditions in a greenhouse for so long that it has subjected germination and plant growth take place, the containers of the soil are checked for plant growth and damage examined and compared with the containers that the unsprayed, sown soil contain. The extent of damage or killing is given with numbers from 0 to 10 rated, with the rating 0 showing no damage or destruction and the rating 10 100 C / ige damage or kill-mean.

Table I Leaf Spray Test Soil Germination Test Comp. Soy example Men- Gra- Tree- Toma- Days- Men- boh- Gra Tree-No. millet num mustard wanted tes millet num mustard wool 1 1 2 0 2 6 5 0 2 10 2 0 2 4 10 8 2 9+ 10 10 10 20 10 10 0 10 7 2 1 0 0 0 3 2 0 2 7 0 0 2 0 10 2 1+ 2 8 1 2 20 10 10 0 7 2 3 1 0 0 0 0 1 0 2 2 0 0 0 0 10 3 10 5 2 4 0 20 10 0 0 1+ 1 4 1 0.0 0 0 0 0 2 0 0 0 0 0 10 3 2 4 3 1 2 20 10 4 4 0 0 5 1 0 2 0 1 0 0 2 0 0 0 0 1 10 6 9 6 4 4 0 20 10 6 1 6 2 6 1 0 0 7 5 5 6 2 10 3 0 5 0 10 5 6 9 9 10 9 20 10 8 3 10 7 7 1 3 5 0 4 1 0 2 0 0 0 0 0 10 10 10 10 10 10 6 20 0 5 2 9 4 8 1 0 0 6 2 0 5 2 0 0 0 6 0 10 9 9 10 8 10 10 20 10 9 2 10 2 9 1 5 0 5 2 7 2 2 4 0 0 0 0 10 8 10 10 10 10 10 20 10 10 2 10 0 10 1 0 0 0 0 0 0 2 1 0 0 0 0 10 8 7 9 6 10 9 20 9 8 6 2 2 11 1 2 2 0 2 1 1 2 0 0 0 0 0 10 10 10 9 7 10 9 20 9 9 0 1 3 12 1 2 0 2 0 0 0 2 0 0 0 0 0 10 9 8 8 8 10 9 20 1 10 3 0 7 13 1 0 0 0 0 1 0 2 0 0 0 0 0 10 9 10 9 5 10 6 20 4 10 0 0 0 14 1 0 1 0 0 0 0 2 0 0 0 0 0 10 8 6 9 9 9 1 20 2 9 0 0 2 Table I. (Continued) Leaf spray test Soil germination test Comp. Men- Gra- Tree- Toma Days- Men soy tree example millet num mustard wolle ten tes boh- grass wool no. millet num mustard 15 1 4 4 0 0 0 1 2 0 0 0 0 0 10 10 9 10 8 10 10 20 7 6 0 2 3 16 1 3 0 2 0 1 0 2 2 0 1 2 0 10 7 9 9 8 8 6 20 10 4 3 8 0 17 1 2 0 0 2 2 2 2 0 0 0 0 0 10 8 1 9 6 9 7 20 6 2 2 0 0 18 1 0 0 0 1 1 0 2 1 0 0 0 0 10 2 1 9 5 9 4 20 5 4 2 3 0 19 1 2 0 0 3 0 0 2 0 0 0 0 0 10 5 4 9 6 10 7 20 1 2 2 0 0 20 1 0 2 0 2 2 0 2 1 0 0 0 0 10 5 5 7 4 10 3 20 2 0 0 0 0 Table I (continued) Leaf spray test soil germination test conn. Men- Gra- Tree- Toma- Days- Men- Soy- Gram tree example millet num mustard wool tes boh num wool num millet Mustard 21 1 0 3 4 0 0 0 2 1 0 0 0 0 10 9 9 10 8 9 8 20 9 4 1 3 0 22 1 0 0 4 3 4 2 2 2 0 0 0 0 10 5 1 9 8 9 7 20 8 8 2 4 3 23 1 2 1 2 2 2 2 2 3 6 0 3 0 10 8 8 10 7 9 4 20 3 10 9 10 6 24 1 3 1 0 5 0 0 2 2 9 2 0 0 10 9 9 8 6 9 2 20 7 10 10 2 0 25 1 0 0 0 2 0 1 2 0 0 0 1 0 10 5 10 5 6 7 2 20 3 10 4 4 0 26 1 0 0 0 2 1 0 2 2 10 2 0 0 10 10 10 7 10 10 6 20 10 10 10 2 0 27 1 2 1 1 2 0 0 2 0 2 0 0 0 10 9 9 10 5 10 8 20 10 10 4 2 0 Table I (continued) Leaf Spray Test Soil Germination Test Connection Soy example Men- Gra- Tree- Toma days- Men- boh- Gra Tree no. ge millet num mustard wanted millet num mustard wool 28 1 0 1 1 1 0 0 2 2 0 0 0 0 10 10 10 10 9 10 10 20 8 9 0 3 0 29 1 0 0 1 0 0 0 2 0 0 0 0 0 10 9 10 10 3 10 10 20 4 5 0 0 0 30 1 4 0 3 2 0 0 2 1 2 0 0 0 10 8 10 9 9 10 8 20 8 4 0 7 2 31 1 0 0 0 0 0 0 2 0 0 0 0 0 10 10 10 10 5 10 10 20 0 0 0 7 9 32 1 4 0 0 0 0 0 2 0 0 0 1 0 10 9 10 8 5 10 8 20 9 4 0 7 0 33 1 2 2 1 2 0 0 2 0 0 0 2 5 10 8 10 9 7 10 1 20 6 2 0 3 6 34 1 3 8 5 2 2 0 2 6 9 0 0 0 10 10 10 10 10 10 10 20 8 10 10 2 0 35 1 1 1 2 2 0 0 2 2 8 0 1 3 10 9 10 10 5 10 8 20 9 10 8 10 4 36 1 8 4 5 4 4 1 2 0 10 0 0 0 10 9 9 10 8 10 8 20 9 10 8 6 4 37 1 10 0 2 2 2 2 0 10 3 1 0 10 9 9 9 9 10 5 20 7 10 9 9 8 38 1 0 0 2 0 1 0 2 6 9 0 0 0 10 6 10 7 5 9 4 20 7 10 0 0 0 39 1 0 2 0 0 0 0 2 5 10 0 0 0 10 5 8 9 5 8 3 20 3 10 1 9 4 40 1 0 0 0 2 2 0 2 0 0 2 0 0 10 8 8 8 8 9 3 20 10 4 3 1 0 41 1 0 2 1 0+ 2 0 2 0 0 1 0 0 10 4 9 5 1 10 3 20 1 4 2 0 4 42 1 0 0 0 0 0 0 2 2 3 0 0 0 10 6 10 6 2 6 6 20 9 10 4 2 0 Tabel I (continued) Leaf spray test Soil germination test Comp.

Soy Example Men Gra Tree Toma Days Men Gra Tree Beans No. ge millet num mustard wool tes ge millet num mustard wool 43 1 3 2 0 0 0 0 2 0 0 0 0 0 10 5 10 2 3 9 1 20 0 0 0 0 0 44 1 9 10 9 8 10 6 2 0 0 0 0 0 10 10 10 10 10 10 10 20 0 2 0 8 0 45 1 0 6 5 0 4 0 2 0 0 0 0 0 10 9 10 9 6 10 10 20 0 0 2 8 0 46 1 0 3 0 0 0 1 2 0 0 0 0 0 10 6 10 7 6 4 9 20 3 10 0 0 0 47 1 2 2 0 0 3 1 2 0 0 2 0 0 10 9 10 4 2 6 7 20 3 6 4 0 0 48 1 3 3 0 1 0 0 2 0 5 0 0 0 10 9 10 10 10 10 3 20 6 10 4 3 2 49 1 10 10 10 8 10 10 2 1 1 0 0 0 10 10 10 10 10 10 10 20 6 9 5 10 0 50 1 10 6 10 10 10 10 2 0 1 3 0 0 10 10 10 10 10 10 10 20 8 10 6 10 0 51 1 7 7 0 0 2 2 2 0 2 0 0 0 10 9 10 10 10 10 10 20 1 9 4 6 8 52 1 7 6 0 1 1 0 2 4 0 0 0 0 10 10 10 10 10 10 10 20 6 8 0 7 7 53 1 4 3 2 1 0 0 2 2 0 3 0 0 10 10 10 10 10 10 10 20 5 10 2 6 2 54 1 9 0 4 4 2 4 2 0 0 6 2 0 10 9+ 10 10 9 9 9 20 10 1 2 8 4 55 1 3 3 0 2 0 0 2 4 0 5 0 0 10 10 10 10 10 10 10 20 10 10 3 6 1 Tabel I (continued) Leaf spray test Soil germination test Comp. Soy Example Men- Gr- Tree Toma Days Menboh Gra Tree No. Millet and mustard wanted to go down Millet num mustard wool 56 1 2 3 1 5 0 2 2 3 0 0 1 0 10 10 10 10 10 10 10 10 20 10 5 2 5 0 57 1 8 6 2 6 9 3 2 4 10 3 1 0 10 10 10 10 10 10 10 10 20 10 10 10 8 3 71 1 9 2 9 1 4 2 2 6 10 9 8 0 10 10 10 9 9 8 6 20 10 10 10 10 10 72 1 5 2 2 0 3 0 2 2 10 9 0 0 10 10 8 10 6 6 4 20 7 10 10 9 1 73 1 0 2 0 0 0 0 2 10 9 0 0 0 10 6 10 7 3 0 0 20 10 10 0 7 3 74 1 3 3 1 0 2 0 2 0 10 10 1 4 10 10 10 10 9 8 7 20 9 10 10 10 5 75 1 5 2 1 0 1 2 2 0 10 8 9 1 10 10 10 10 4 8 6 20 9 10 10 3 Examples 76-82 These examples describe specific embodiments of the combined herbicidal agents of the invention.

The general recipe for these embodiments is the same as in Examples 1 to 75.

All combined herbicidal agents are made so that one the components at 20-250 C to a phyto-toxic mixture of any concentration mixed. With this mixture, the area to be treated becomes the desired Application concentration sprayed.

The components of the phytotoxic mixture of each example that relative weight ratio of the constituents, the fruit or fruit for which each specific means is particularly suitable, the time of application (before = before Emergence; after = after emergence) and the recommended application quantities on the phytotoxic mixture are given in Table II.

Table II For- Ingredients- Weight lost parts of the ratio no. Phytotoxi- the time of the quantity components fruits application weeds (kg / hectare) mixed 76 product of 1: 1-2: 1 Hordeum before Bromus tectorum 0.84-4.48 manufacturing Granum Foxtail *) method II Cotton Amaranthus Norea Peanuts Avena Syricum (granum) Lolium soybeans Mollugo verticillata peas Echinochloa crusgalli green Beans Digitaria sanguinelis Wheat Brassica Cassia marylandica Cissampelos pareira Euphorbia Portulaca 77 product of 1: 1.2 cotton in front of shower tail *) 2.46 manufacturing Peas Echinochloa crusgalli method II Peanuts Digitaria sanguinelis Fluometuron Avena Brassica Cassia marylandica Cissampelos pareira Sida spinosa Annual Ipomoea Amaranthus Euphorbia Portulaca 78 Product of 1: 1-2: 1 soybeans after (zei- Digitaria sanguinelis 2.24-3.36 Production time, if green foxtail *) process II the grasses Echinochloa crusgalli Chloroxuron 1 to 2 leaves Amaranthus ter and one Brassica height of 2.5 cm) *) Alopecurus, Hordeum or Setaria Tabel II (continued) In- constituent parts by weight of the ratio no. Phytotoxi- der Time of quantity Ingredients Fruits Application Weeds (kg / hectare) Mix 79 product of 2: 1-1: 2 ways before Avena 0.84-2.24 manufacturing cotton Digitaria sanguinelis method II soybeans Echinochloa crusgalli Diuron Granum Amaranthus Chenopodium album Lolium Bromus tectorum Sida spinosa 80 Product of 2: 1-1: 2 wheat before Cissampelos pareira 0.84-1.68 manufacturing cotton Brassica juncea crispifolia method II Soybeans Cassia marylandica Linuron Granum Datura stramonium foxtail *) Lolium Bromus tectorum Product of 0.4: 1-1.2: 1 granum before Digitaria sanguinelis 0.56-1.12 manufacturing cotton foxtail *) proceed II soybeans Echinochloa crusgalli Fenuron Sida spinosa Cissampelos pareira Amaranthus Chenopodium album Brassica juncea crispifolia Ipomoea 81 Product of 12: 1-1: 1 Granum Proceed according to Setaria italica 0.56-3.36 manufacturing Syricum stramineofruchta II (granum) Digitaria sanguinelis Atrazine green foxtail *) Echinochloa crusgalli Amaranthus Brassica *) Alopecurus, Hordeum or Setaria Tabel II (continued) In- constituent parts by weight of the ratio no. Phytotoxi- der Time of quantity Ingredients Fruits Application Weeds (kg / hectare) Mix 82 product of 1: 1-1: 4 peas before and Digitaria sanguinelis 3.36-6.72 manufacturing Process red beets after green foxtail *) II Sugar beet Echinochloa crusgalli Pyrazon Brassica Datura stramonium Cissampelos pareira Ambrosia *) Alopecurus, Hordeum or Setaria Obtained in the practice of the invention, typical results are compiled in the tables below. These results were obtained in standard greenhouse and field trials. The results these attempts are in most cases expressed as a percentage reduction in growth in the case of application before emergence and as percentage kill or damage indicated in the case of application after emergence. In all of these attempts are the results have been obtained by mixing the treated areas with untreated Control areas at pre-emergence application and the treated plants compared with untreated control plants when applied after emergence Has. In the following tables, "lsgW / ha" means kilograms of active ingredient per hectare, a synergism is assumed if the numerical values obtained when the results are significantly larger than those expected according to the equation E = x '+ y - are obtained, in which x is the percentage reduction in growth or the percentage of destruction or damage caused by the herbicide A at p kg per ha, y the percentage reduction in growth or percentage kill or Damage by the herbicide B at q kg per ha and E the expected percentage Reduction in growth or percentage killing or damage by the herbicides A and B at p + q mean kg per ha. The basics and the accuracy of this Equation are described in "Weeds", 15, pages 20-22 ..

Table III contains data that were used prior to emergence at Field experiments with N-Chbracetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Norea, Fluometuron, mixtures of the ester with Norea and mixtures of the ester with Fluometuron have been received. Table III Cut through Cas-Cis-Sida Bras-sia sample- spi-phytotoxic amount fox- Echinochloa Digitaria Ave- Grä- sica mary- los nosa material (kgW / ha) tail **) crusgalli sanguinelis na ser lan- pardica eira N-chloroacetyl- 1.12 94 99 65 89 7 7 12 0 N- (2,6-diethylphenyl) -glycine- 2.24 99 100 100 72 93 6 7 20 7 ethyl ester Norea 1.68 70 71 97 62 75 77 66 85 0 ester + Norea 1.12 + 1.68 99 99 100 90 *) 97 90 *) 70 90 30 *) 2.24 + 1.68 96 100 100 90 *) 96 88 *) 33 73 38 *) fluorometuron 1.34 87 75 97 90 87 100 94 92 100 ester + fluorometuron 1.12 + 1.34 100 97 100 95 98 100 99 96 100 *) Synergistic result **) Alopecurus, Hordeum or Setaria Table II (continued) Average broad- Medi-phytotoxic amount of one-year- Amaran- Eu- burdock Portu- blättri- Gurcago soil material (kgW / ha) rige thus phorbia *) laca ge toad sati- nuts Ipomoea herbs va N-chloroacetyl- 1.12 5 95 71 5 90 32 10 0 4 N- (2,6-diethylphenyl) -glycine- 2.24 2 100 89 7 100 38 30 10 7 ethyl ester Norea 1.68 25 91 74 12 100 59 82 77 2 ester + Norea 1.12 + 1.68 4 100 95 32 100 68 75 76 0 2.24 + 1.68 15 99 92 32 100 63 60 75 2 fluometuron 1.34 75 100 97 19 100 86 97 100 50 Ester + Fluometuron 1.12 + 1.34 81 100 99 22 100 89 77 100 26 *) Xanthium or Arctium Table III (continued) Lathyrus green soy syri phytotoxic amount of odo- white boh tree boh cum sugar material (kgW / ha) ratus zen nen rice wool (granum) Granum beet 5 5 0 25 5 0 4 5 0 N-chloroacetyl- 1.12 N- (2,6-diethylphenyl) -glycine- 2.24 11 11 1 41 0 0 24 0 6 ethyl ester Norea 1.68 12 31 5 54 7 0 0 4 80 Ester + Norea 1.12 + 1.68 7 30 30 74 0 14 4 11 90 2.24 + 1.68 10 45 27 68 1 2 19 7 98 Fluometuron 1.34 26 55 82 82 6 37 26 10 100 Ester + Fluometuron 1.12 + 1.34 22 65 83 89 11 49 45 40 100 In Table IV are in use before emergence in the greenhouse with N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Results obtained with regard to Norea and mixtures of these two active ingredients der.weed control and wheat tolerance compiled.

In Table V results are compiled that were used before the emergence in the greenhouse with N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Norea, diuron, linuron and mixtures of the ester and diuron and mixtures of the ester and linuron have been obtained.

Table VI summarizes the results that were obtained when using after emergence in field trials with soybeans using N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Ohloroxuron sojie mixtures of these two active ingredients have been obtained, In this table,? 1FN? 1 means that the application should be applied early after emergence, i.e. at a time when the grasses have 1 to 2 leaves and 2.5 cm in height, has occurred, while "N" means post-emergence application is when the grasses have 3 to 4 leaves and a size of 5 to 7.5 cm.

In Tables VII and VIII are in the greenhouse with N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Linuron and mixtures of these two active ingredients when used as pre-run herbicides obtained results compiled. A rating of 0 means no kill or damage or inhibition of growth and a rating of 10 means 100% kill or damage or inhibition of growth.

Table IV% Weed Control Brassi- Setaria ca jun- italica Echino- Agrocea cri- strami- cloa stemma Bromus% wheat phytotoxic amount spifolia neufruc-crus- githa- tecto- Schadi material (kgW / ha) ta galli go rum Avena gung N-chloroacetyl-N- 0.56 0 97 97 0 35 80 0 (2,6-diethylphenyl) glycine ethyl ester Norea 0.56 0 45 80 0 10 35 16 1.12 60 97 100 15 60 70 38 Ester + Norea 0.56 + 0.56 40 *) 100 97 45 *) 85 *) 90 16 0.56 + 1.12 95 *) 100 100 45 *) 97 *) 100 0 *) Synergistic result Tabel V% control Phytotoxic amount of material (kgW / ha) Lolium Bromus tectorum N-Chloracetyl-N- 0.42 0 10 (2,6-diethylphe-0.84 70 82 nyl) -glycine ethyl ester Norea 0.42 50 43 0.84 80 90 Ester + Norea 0.42 + 0.42 80 *) 58 *) 0.84 + 0.42 98 *) 72 0.42 + 0.84 93 *) 90 0.84 + 0.84 95 75 Diuron 0.42 20 15 0.84 85 28 Ester + Diuron 0.42 + 0.42 17 33 *) 0.84 + 0.42 83 70 0.42 + 0.84 57 75 *) 0.84 + 0.84 93 80 Linuron 0.42 0 3 0.84 20 20 Ester + Linuron 0.42 + Q, 42 57 *) 55 *) 0.84 + 0.42 87 *) 62 0.42 + 0.84 63 *) 72 *) 0.84 + 0.84 85 *) 60 *) Synergistic result Table VI% Weed Control Digita- green Echinoria san- Fuchs- chloa Ama-Phytotoxic amount Anwen- guine- tail crus- ran Brassi-% soybean material (kgW / ha) dung lis **) galli thus ca damage to N-chloroacetyl- 1.12 FN 25 25 0 18 0 0 N- (2,6-diethyl- 2.24 38 62 72 30 0 0 phenyl) glycine ethyl ester chloroxuron 1.12 FN 60 92 85 100 100 35 2.24 96 94 97 99 100 80 Ester + Chloroxuron 1.12 + 1.12 FN 80 *) 88 80 100 100 25 2.24 + 1.12 98 *) 90 98 100 100 48 Ester 1.12 N 0 10 28 35 18 0 2.24 N 30 5 42 75 0 0 Chloroxuron 1.12 N 42 45 55 100 98 65 2.24 82 58 52 100 100 42 Ester + 1.12 + 1.12 N 62 *) 75 *) 100 100 48 Chloroxuron 2.24 + 1.12 82 *) 78 *) 100 100 48 *) Synergistic result **) Alopecurus, Hordeum or Setaria Table VII Echino Digi- Cissamchloa taria Sida pelos Brassica Phytotoxic amount crusgal- sangui- Ipo- spi- parei- day- juncea material (kgW / ha) li nelis moea nosa ra tes crispifolia N-chloroacetyl 0.42 10 8 0 6 0 4 0 N- (2,6-diethylphenyl) glycine ethyl ester linuron 0.42 3 3 1 1 10 2 10 0.84 8 10 5 10 10 6 10 Ester + Linuron 0.42 + 0.42 10 9 0 8 *) 10 3 10 0.42 + 0.84 10 10 1 10 10 4 10 Cassia Datura Table VII Phytotoxic amount mary stra Syricum soy tree (cont.) material (kgW / ha) landica monium (granum) beans wool N-chloroacetyl 0.42 2 2 3 0 2 N- (2,6-diethylphenyl) glycine ethyl ester Linuron 0.42 10 7 1 0 0 0.84 10 10 0 0 2 Ester + Linuron 0.42 + 0.42 8 7 6 0 2 0.42 + 0.84 10 8 9 0 2 *) Synergistic result Table VIII Phytotoxic Amount of soy tree Syricum Sida Amaran material (kgW / ha) bean wool (granum) Granum Ipomoea spinosa thus N-chloroacetyl-0.56 0 3.0 5.5 2.0 0 5.0 8.5 N- (2,6-diethylphenyl) glycine ethyl ester Linuron 0.28 2.5 4.0 2.5 0 0 3.0 10.0 0.56 0 0 1.5 0 0 10.0 10.0 Ester + 0.56 + 0.28 5.5 2.5 7.5 0 1.5 1.5 10.0 Linuron 0.56 + 0.56 0 1.0 5.0 1.5 1.5 9.5 10.0 Table VIII (continued) Brassica Phytotoxic Amount Echinochloa Fuchs- Cissampelos juncea material (kgW / ha) crusgalli tail **) pareira crispifolia Avena N-chloroacetyl- 0.56 10.0 9.5 4.0 2.5 3.5 N- (2,6-diethylphenyl) glycine ethyl ester Linuron 0.28 0 5.0 7.0 00 0.56 3.0 7.0 10.0 8.0 1.5 Ester + 0.56 + 0.28 10.0 10.0 6.5 7.0 10.0 * ) Linuron 0.56 + 0.56 10.0 10.0 9.5 8.5 9.0 *) *) Synergistic result **) Alopecurus, Hordeum or Setaria Table IX summarizes the results those in the greenhouse using N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Diuron, linuron and mixtures of the ester and diuron and mixtures of the ester and linuron as a precursor herbicide. A rating of 0 means no kill, damage or inhibition of growth and a rating number of 10 means 100% destruction, damage or inhibition of growth.

In Table X results are summarized, which in the greenhouse under Use of N-chloroacetyl-N- (2,6-diethylphenyl) glycine ethyl ester, fenuron and Mixtures of these two active ingredients have been obtained as first-line herbicides. A rating of 0 means no damage or destruction or inhibition of the Growth and a rating of 10 100% damage or killing or inhibition of growth.

In Table XI results are compiled, which in the engine house under Use of N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, atrazine as well Mixtures of these two active ingredients as follow-up herbicides in the fight against welschem Fennich (Setaria italica stramineofructa).

Table IX Digi- Echino-Cheno-Medi- Zuk-Bromus taria chloa Amapodium cago soy ker phytotoxic amount of white ave tectosangui- crusran album sati tree boh- rü material (kgW / ha) zen na rum nelis galli thus va want to use N-chloroacetyl 0.56 0 9 4 10 10 5 3 5 0 0 0 N- (2,6-diethylphenyl) glycine ethyl ester diuron 0.28 3 4 2 5 0 10 7 3 0 0 6 0.56 5 5 1 10 5 10 10 4 0 0 8 Ester + 0.56 + 0.28 0 10 5 10 10 10 10 *) 10 *) 0 - 7 Diuron 0.56 + 0.56 0 10 3 10 10 10 10 10 *) 0 2 8 Linuron 0.28 0 0 3 9 0 9 10 5 0 0 7 0.56 00 1 9 5 10 10 10 0 3 8 Ester + 0.56 + 0.28 3 10 0 10 10 10 10 10 *) 0 3 9 Linuron 0.56 + 0.56 3 9 5 10 10 10 10 10 0 0 9 *) Synergistic Result Table X Digi- Echinotaria Fuchs- chloa Cissam-Phytotoxic Amount of tree soy sangui- tail crus- Sida pelos material (kgW / ha) Granum wool beans nelis *) galli spinosa pareira N-chloroacetyl 0.42 0 0 0 7 10 9 1 0 N- (2,6-diethylphenyl) glycine ethyl ester Fenuron 0.17 0 0 0 1 1 2 8 10 0.34 0 0 3 6 5 6 10 10 0.50 2 1 4 7 6 6 9 10 Ester + 0.42 + 0.17 0 0 3 8 10 9+ 8 10 Fenuron 0.42 + 0.43 3 1 2 9 10 9+ 10 10 0.42 + 0.50 4 1 6 10 10 9+ 10 10 Table X (continued) Phytotoxic Amount Brassica juncea Material (kgW / ha) Amaranthus Chenopodium album crispifolia Ipomoea N-Chloracetayl- 0.42 8 0 0 0 N- (2,6-diethylphenyl) glycine ethyl ester fenuron 0.17 9 9 10 6 0.34 9+ 10 9+ 8 0.50 10 9+ 10 8 Ester + 0.42 + 0.17 10 9+ 10 1 Fenuron 0.42 + 0.34 10 9+ 10 8 0.42 + 0.50 10 9+ 10 9 *) Alopecurus, Hordeum or Setaria Tabel XI Phytotoxic amount of material (kgW / ha) Test # 1 Test # 2 N-Chbracetyl-N- 0.56 20 26 (2,6-diethylphenyl) - 0.84 61 38 glycine ethyl ester atrazine 0.07 18 19 0.14 74 50 Ester + atrazine 0.56 + 0.07 75 *) 79 *) 0.84 + 0.07 83 *) 77 *) 0.56 + 0.14 85 * 9950 ** 0.84 + 0.14 88 *) Synergistic result In Table XII are the results compiled, the field test with N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, Atrazine and mixtures of these two active Syricum (granum) substances as follow-up herbicides for weed control at / have been received. In Table XII, "FN" means that the application early after emergence, i.e. when the grass has 1 to 2 leaves and have a height of 2.5 cm, while "N" means that the application after emergence is done at a time when the grasses have 3 - 4 leaves and have a height of 5 - 7.5 cm.

Table XIII summarizes the results obtained in the field test with N-chloroacetyl - (2,6-diethylphenyl \ glycine ethyl ester, pyrazone and mixtures from these two active ingredients as first-line herbicides for weed control Peas and beets have been obtained.

Table 'XIV summarizes the results obtained in the field test with N-chloroacetyl-N- (2,6-diethylphenyl) -glycine ethyl ester, pyrazone and mixtures obtained from these two active ingredients for weed control in sugar beet have been. -In the table, "before" and "after" mean use as a pre-run herbicide or follow-up herbicide. Table XII% Weed Control Digitaria green Echino-% Syricum Phytotoxic amount of application sanguine- fox chloa amaran- Bras (granum) material (kgW / ha) dung lis tail **) crusgalli thus sica damage N-chloroacetyl 1.12 FN 25 25 0 18 0 0 N- (2,6-diethyl-2.24 38 62 72 30 0 0 phenyl) -glycine ethyl ester Atrazine 1.12 FN 48 85 68 100 100 5 Ester + Atrazine 1.12 + 1.12 FN 90 *) 99 *) 98 *) 100 100 0 2.24 + 1.12 FN 100 *) 99 *) 100 *) 100 100 32 Ester 1.12 N 0 10 28 35 18 0 2.24 N 30 5 42 75 0 0 atrazine 0.56 N 65 42 48 100 100 0 1.12 N 85 82 80 100 100 0 ester + Atrazine 1.12 + 0.56 N 88 *) 82 *) 62 100 100 15 2.24 + 0.56 N 92 *) 88 *) 96 *) 100 99 0 1.12 + 1.12 N 84 65 90 *) 100 100 15 2.24 + 1.12 N 98 *) 98 *) 99 *) 100 100 45 *) Synergistic Result **) Alopecurus, Hordeum or Setaria Table XIII% Fruit% Weed control dami-Cheno- Datura Cissam- gung Phytotoxic amount annual podium stra- pelos Ambro- Amaran- Erb- Red material (kgW / ha) grasses album monium pareira sia thus sen beets N-chloroacetyl- 1.12 98 0 0 - 0 95 0 0 N- (2,6-diethyl 2.24 100 20 0 - 0 100 0 13 phenyl) glycine ethyl ester pyrazone 2.24 75 100 67 100 100 98 0 27 4.48 87 100 98 - 0 58 100 5 10 ester + 1.12 + 2.24 52 85 - 0 58 100 5 10 pyrazone 1.12 + 4.48 96 98 100 100 100 100 35 37 2.24 + 2.24 94 88 100 100 100 100 37 20 Tabel XIV% Weed Control Cheno-Phytotoxic Material Amount Application- podium Ambro- annual% sugar beet (kgW / ha) dung album sia grass damage N-chloroacetyl-N- (2.6- 1.12 Before 25 0 99 0 diethylphenyl) glycine 2.24 "12 0 100 0 ethyl ester 4.48" 0 0 100 0 pyrazone 4.48 "99 100 99 0 ester + pyrazone 1.12 + 4.48" 97 100 99 3 2.24 + 4.48 "98 96 99 5 Esters 1.12 After 7 0 100 0 2.24" 0 0 100 0 4.48 "0 0 100 0 Pyrazone 4.48 "88 100 86 0 Ester + Pyrazone 2.24 + 2.24" 98 100 100 0 2.24 + 4.48 "98 *) 100 100 0 *) Synergistic result From the data of the previous Tables show that the various embodiments of the phytotor smell Materials of the invention effective against many, both grassy and broad-leaved, Weeds are while many crops tolerate them.

In addition, these embodiments show synergistic, phytotoxic Effects on a wide variety of weeds, which are in the special interest; used expression "consisting essentially of", excludes the use of substances not mentioned at a concentration which is so high that there is essentially an adverse effect Influence of the essential properties and characteristics of the defined herbicides Means takes place while the presence of one or more not listed Substances in long concentrations which are so low that no significant disadvantageous Influencing of the essential properties and characteristics takes place, permissible is.

Preferably, the herbicidal compositions of the invention are used in an amount from 0.16 to 5.60 kg / hectare, based on the active ingredient, applied.

According to a preferred embodiment, the herbicidal agents contain the invention additionally as a complementary herbicidal compound Norea, Fluometuron, Chloroxuron, diuron, linuron, fenuron, atrazine or pyrazone, preferably in one Weight ratio to the N-phenylamine of 4: 1 to 1:12. In this case, it is preferred the combination of the N-phenylamine and the complementary herbicidal compound selected to be synergistically phytotoxic to at least one of the weeds works. According to another preferred embodiment, the control takes place of grassy and broad-leaved weeds the application of the complementary herbicidal compounds were separate from N-phenylamine, but about the same Time like this.

Claims (3)

Claims N-substituted N-phenylamines of the general formula (I) in which the substituents R are identical or different and represent a hydrogen or halogen atom, a nitro or trihalomethyl group, a C1-7-alkyl or C1-7-alkoxy radical, R 'a hydrogen atom, a mono-, di- or trihaloacetyl group is, R "is a C1-7-alkylene or C2-7-alkylidene radical and Q is a carboxyl group, a salt or a C1-7-alkanol ester thereof, an amide, mono- or disubstituted amide radical, the substituents C1-7 -Alkyl radicals or aryl radicals sand, or a carbohydrazide or substituted carbohydrazide radical with C1-7-alkyl radicals or aryl radicals as substituents. 2. Amines according to Claim 1, characterized in that the substituents R in the 2- and 6-positions have the meaning C2H5, the remaining substituents R the meaning H, R 'the meaning H or C1-CH2-C10, R1 Have C '° -C2H5- the meaning CH2 and Q the meaning 3. Herbicides, the application aids and contain an effective amount of phytotoxic material, characterized in that that the phytotoxic material contains a compound according to claim 1 or 2.